Getting courted for a new gig

Start up, about two years in. Valuable IP/tech.

High pay and equity, but high risk. It is a feast or famine type deal. Either ill be retired in 3-5 or wishing I never did it.

I have a few months to learn more and mull it over. Everyone is flying here in a few months to have a dinner and make an offer (hopefully).

I am torn because my quality of life right now is awesome.

Just remember… The Google guys wanted an actual chef to run their cafeteria, but couldn’t afford it. They eventually had one take stocks instead of his requested salary. He’s a multimillionaire now.

Then again remember Theranos recruited some ridiculous amazing people.

Yeah, I’m no help…

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Nice position to be in. Options are good. Perhaps the decision will become more clear over the next weeks but I think you will have to take a leap one way or another. Best of luck.

It is coming through a close friend, so I get the luxury of mulling it for a bit. I wouldn’t start until Jan1 or so if it worked out.

I don’t know if I want to go into 3-5 yrs of a hard hustle and grinding it out. I’m a bit tired lol.

Sounds like you’re getting in on the ground floor and will be a very early employee number. A couple of questions to ask yourself:

  • What’s the company’s funding look like? Self-sustaining? On their Series A it sounds like, do they have Series B lined up, or at least thinking about it?
  • What’s the company’s exit strategy? What does the space look like? Who are the competitors big and small? Can the big guys pivot and take over the space you guys are carving out?
  • What are you missing out potentially by taking this offer vs [presumably] a bigger company? Not just compensation, but in terms of career path as well.
  • If things don’t pan out, and the company folds before it can get Series B (let’s say), can you easily find another gig in your space and locale?

If you’ve never worked for a small startup before, that might be an incentive to give it a shot. No regrets and all that.

And then, a trick someone gave me when I was in a similar situation. I had to decide between two positions over a weekend: Take one day and decide you’re going for Position A. Trick your mind into ‘making the decision’. Then on the next day, force your mind to decide you’re taking Position B. Really commit your mind to ‘deciding’.

It sounds a little weird, and not everyone can do it. But it was worked great for me. As Position A was on paper the better option. But once I “made the decision” I was riddled with anxiety about the people I would be working with, the technical baggage/debt I would have to deal with. Whereas with Position B I became happy and optimistic for the future. I went with B and it’s been great.

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5 employees. I would make 6.

Funding isn’t an issue. Very few investors, committed capital is more than what is needed for the next 3 yrs. They are optimistic about their rev projections, and if I cut them by 50% it still looks good.

Exit strategy is a sale of the company and everyone is done. This is their third time doing this, the last two were sold.

What am I missing out on? I make less now than I would make with them, but have solid job security. Further upside is limited, but my quality of life is 9/10 right now.

If I lose my job I likely have to movie to Palm Beach or Miami.

Would this job require you moving again? What are the downsides? Less time with your toes in the sand and line in the water?

It sounds like a choice between two good options. Those are the toughest to make. It really depends on you then, if you’re up for the grind of a startup vs leaving well enough alone.

Try the trick I mentioned above on “Making the Decision” on different days. I know it sounds odd, but if you can make your mind do it, it’ll really help in your decision making. Sounds like potential for lifestyle changes (more work hours and stress), so important to weigh all factors.

Startups are typically a young man’s game (in terms of hours and risk). Otoh, it sounds like you have a plum opportunity dropped in your lap, and you’ll be kicking yourself later when everyone cashes out and you missed out. Tough call!

Yeah, it would be a 3-5 yr high pressure grind.

So less time doing my daily nonsense like writing, fishing, yoga, and cooking. Life would become much more work centric.

It sounds like you’ve worked hard to get where you are now. You seem pretty happy with your life after the move to Florida. That would be hard to give up.

The “if it works out, I retire in 3-5” part makes it sounds too good to be true. But, opinions are like assholes, etc

No one on their death bed ever said they wished they had worked more or earned more money, best of luck with whatever you decide

What would you do with the extra money you get from the proposed new job? In your 3-5 year analysis, how much more money would it be than staying where you are? You say your quality of life is 9/10 right now. Sounds like you’re happy and liking your job. If you had to stay at your current situation for 10 years before you have enough to retire like you want, do you think those years will be unbearable? Does having that much more money while working more bring your quality of life to a 10/10?

I am basing the likelihood on the valuation they did their last round at and an offer that they turned down for the entire operation.

It isn’t guaranteed, and would be 50/50 at best, but I would likely be sitting on the beach and out of this dreadful industry by 45.